What does it mean to be an entrepreneur? For Minneapolis-based rapper, social entrepreneur and record label president Dessa, entrepreneurship means the ability to spread her passion – her music and writing – with as many people as she can. Over the course of her more than 10-year career, she’s performed at top music festivals, including SXSW, Lallapalooza, Montreal Jazz Festival and Glastonbury, and in 2017 she’ll bring her unique music to a full evening’s performance with the Minnesota Orchestra.

Chosen to be a speaker at Mayo Clinic’s Transform Conference, focused on innovation, in September 2016, she shares her entrepreneurial journey: “I was a medical technical writer by day, a waitress by night, a rapper by night-night.” Her three-shift approach to getting started as a musician has paid off, and she has much to share for aspiring entrepreneurs, musicians or anyone with an idea.

Dessa grew up in South Minneapolis and attended the University of Minnesota, where she received a philosophy degree. Realizing there was no clear-cut track for aspiring philosophers, she found art and music as her outlet to leverage this skill set. But before she could sustain her life on music alone, the then 20-year-old college graduate worked as a medical technical writer in the health care industry. She describes the feeling of working in a professional realm as highly intimidating, “I was terrified and excited. I was sensitive about my age – I wore my mother’s wedding ring and a pager with no batteries to cover it up. I always thought my age would be viewed as a liability.”

But even at her young age, Dessa always had ambition – and grit. She began getting involved in the Minneapolis hip-hop scene, eventually joining Doomtree Records and helping build what the label is today.

As her popularity in the music scene grew, so did her career. When it was time for the Doomtree record label to grow in formality, Dessa stepped into the role of CEO. She shared that this presented a learning curve and recalls, “I had to grow into the nametag that I selected.” She recalls that Doomtree has always positioned itself as a flat organization, with the role of CEO being a formality, but despite this, she found a knack for business – helping the label put together a strategic vision for upcoming albums, tours and events. Now in existence for over 10 years, Doomtree records has seven artists owning and managing the label who have released over 50 records.

After serving as the CEO for six years, Dessa has stepped into the role of president, with Doomtree artist Lazerbeak stepping into the role of CEO, so she could focus on her booming music career. To date, she has released four albums and counting, has landed on the Billboard Top 200 in 2013, and has toured internationally with Doomtree, having performed at clubs, festivals, schools, basement parties, and shelters around the world, “from Warsaw to Johannesburg, Sydney to Montreal.”

Of the many lessons she’s learned along the way, she recalls being in a point of tension regarding her age and her career – “For a long time I felt like I had one foot on each side of the see-saw,” she shares. “I was young for the roles I was filling in corporate America, but I was old as a rapper.”

But she states this did not stop her from moving forward in both career and music aggressively and intentionally – “I was eager to be evaluated on the merit of my work and my ideas. If they’re lousy, tell me. But if they’re good, I’d like to be recognized for that.”

She hasn’t let her age deter her and has moved her dreams forward in both music and social entrepreneurship boldly. In 2015 she was on the cover of the Minnesota Business Magazine as a highlighted entrepreneur under 35 years old, and she has taught as an instructor at the McNally College of Music in Minnesota, sharing her passion for music and her knack for entrepreneurship with others.

There has been no slowing down, no deterrence and no lack of ambition for Dessa and her dreams to make a difference. When asking Dessa how her story could apply to others with an idea or dream, she shares that her advice is “master your craft.” She says that many young entrepreneurs or musicians are so eager to share their work to gain popularity that their commitment to learning and skill mastery often wanes.

And beyond skill mastery, Dessa states that growing your dreams requires a committed lifestyle. “Make your own coffee. Take the bus. When you're just starting out, every hour that you have to spend grinding at a day job is time you take away spending on your craft. Live a life that is inexpensive and keep your time to yourself.”

She’s mastered her craft and has committed her lifestyle to her dream, but she recalls the feedback she received when she left her position in the health care industry years ago. When sharing her ideas and ambitions to join Doomtree with her former colleagues, they evaluated the business model and said it was “a tenuous business model that would never last.”

But Dessa knew that with hard work and ambition, they could make it happen. With 50 records released to date, a growing international fan base and strong ties back to the entrepreneurial community, Dessa recalls this criticism and shares that 15 years later, Doomtree’s strategy has lasted, and it’s not slowing down anytime soon.

I’m a passionate social entrepreneur, writer and product developer. I’ve founded several impact-driven companies, like Tinua and Doc’s Recovery House. As a content strategist and storyteller, I try to uncover the "why" behind great companies, entrepreneurs and activists maki...